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Help Desk Supervisor

Remote / Online - Candidates ideally in
Menomonee Falls, Waukesha County, Wisconsin, 53051, USA
Listing for: SKYGEN
Remote/Work from Home position
Listed on 2026-05-18
Job specializations:
  • IT/Tech
    HelpDesk/Support, Technical Support, IT Support, Systems Administrator
Salary/Wage Range or Industry Benchmark: 60000 - 80000 USD Yearly USD 60000.00 80000.00 YEAR
Job Description & How to Apply Below

What are important things that YOU need to know about this role?

  • Hybrid work environment:
    This position is primarily onsite, working four days per week in Menomonee Falls and one remote day. Regular onsite leadership and team presence are critical.
  • Hands‑on supervisory responsibility:
    Leads a team of six direct reports, balancing people leadership with active involvement in frontline support.
  • End‑to‑end ownership:
    Responsible for daily Helpdesk operations, providing technical support, managing escalations, and serving as part of the after‑hours on‑call support team.
What will YOU be doing for us?

Supervise the helpdesk team to ensure customers receive the highest level of service while achieving and maintaining service level requirements. This position also handles first level escalations, facilitates new hire on‑boarding, training/mentoring and documents processes.

What will YOU be working on?
  • Supervise, lead and coach Help Desk staff.
  • Evaluate and revise help desk processes to improve workflows and service levels.
  • Monitor helpdesk ticketing system data to ensure expected service levels are maintained.
  • Ensure documentation and knowledge base data is kept up to date and procedures are followed by Helpdesk team members.
  • Be the escalation resource for help desk and business personnel. Assist with complex problem resolution.
  • Facilitate communication with appropriate internal and external parties as needed.
  • Maintain HITRUST requirements for endpoints containing protected data (workstations & laptops) inventory.
  • Review HITRUST reports showing software installed on employee machines to identify concerns, including software that needs to be updated/patched.
  • Work in conjunction with Human Resources to interview and hire staff.
  • Develop, and motivate staff. Address a variety of personnel actions including employment, termination, performance reviews, salary reviews, disciplinary actions, training and development plans.
  • Work effectively and collaboratively with business resources to ensure seamless support for all users.
  • Work closely with the Director of IT to collaborate on cross‑functional projects.
  • Foster an environment of continuous improvement and excellence.
What qualifications do YOU need to have to be GOOD candidate?
  • Associate or bachelor’s degree in information technology and/or Helpdesk Support or equivalent technical experience
  • 1+ Years or experience in a leadership role (leading others, leading projects etc.)
  • 3+ years of prior experience in a helpdesk/technical support type of role
  • Proficiency with Microsoft Active Directory
  • Knowledge of or some experience with Intune
  • Proficient with Windows Operating Systems
  • Proficient with Microsoft Office & SharePoint applications
  • Proficient with a Help Desk ticketing system
  • Proficient with supporting employees and employee systems in a medium size organization
  • Strong analytical and technical troubleshooting skills
  • Strong organizational skills
  • Strong written and verbal communication skills
  • Ability to successfully lead and motivate teams
What qualifications do YOU need to have to be GREAT candidate?
  • Associate or bachelor’s Degree in a related field.
  • Previous experience managing a Helpdesk team responsible for supporting multiple organizational departments located in multiple facilities including telecommuter/Work from Home employees.
  • Knowledge of Windows desktop operating systems
  • Knowledge of common ITIL service framework
  • Experience with Service Desk Plus
  • Experience administering, configuring and using Helpdesk ticketing systems
  • Experience supporting employees using a VoIP phone system
  • Experience with Nice Incontact and Ring Central
  • Basic understanding of networking (VLANS, Routing, Switching, PoE, Internet Circuits, WAN data circuits
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